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2',7'-Dichlorofluorescein | CAS 76-54-0
| Catalog Number | A17-0109 |
| Category | Fluorescein FAM |
| Molecular Formula | C20H10Cl2O5 |
| Molecular Weight | 401.20 |
* Please be kindly noted products are not for therapeutic use. We do not sell to patients.
Product Introduction
Classic green fluorescent dye with high photostability and strong signal intensity. Used for oxidative stress detection and fluorescence microscopy.
Chemical Information
Product Specification
Application
Computed Properties
Literatures
Patents
| Synonyms | 2',7'-dichloro-3',6'-dihydroxy-spiro[isobenzofuran-1(3H),9'-[9H]xanthen]-3-one; 2',7'-Dichlorofluorescein; Fluorescein 27; Fluorescein 548 |
| IUPAC Name | 2',7'-dichloro-3',6'-dihydroxyspiro[2-benzofuran-3,9'-xanthene]-1-one |
| Canonical SMILES | C1=CC=C2C(=C1)C(=O)OC23C4=CC(=C(C=C4OC5=CC(=C(C=C35)Cl)O)O)Cl |
| InChI | InChI=1S/C20H10Cl2O5/c21-13-5-11-17(7-15(13)23)26-18-8-16(24)14(22)6-12(18)20(11)10-4-2-1-3-9(10)19(25)27-20/h1-8,23-24H |
| InChIKey | VFNKZQNIXUFLBC-UHFFFAOYSA-N |
| Signal | Warning |
| GHSHazardStatements | H315 (90.91%): Causes skin irritation [Warning Skin corrosion/irritation] H319 (100%): Causes serious eye irritation [Warning Serious eye damage/eye irritation] H335 (100%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation] |
| Precautionary Statement Codes | P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (The corresponding statement to each P-code can be found at the GHS Classification page.) |
2’,7’-Dichlorofluorescein (DCF) is a chlorinated derivative of fluorescein, a compound that is widely used as a fluorescent tracer and dye due to its bright green fluorescence and high quantum yield. Structurally, DCF contains two chlorine atoms attached to the fluorescein backbone at the 2’ and 7’ positions, which influence its optical and chemical properties. DCF itself is generally non-fluorescent until it undergoes cellular processes or chemical reactions that enable its conversion to a fluorescent form. This characteristic makes it useful in various biochemical and analytical applications.
One of the primary applications of 2’,7’-Dichlorofluorescein is in the detection and measurement of reactive oxygen species (ROS) within biological systems. When DCF is oxidized by ROS, it transforms into the highly fluorescent 2’,7’-dichlorofluorescein diacetate (DCFH-DA), making it a valuable tool for monitoring oxidative stress in cells and tissues. This process is crucial for studying the effects of oxidative stress-related diseases and assessing the efficacy of antioxidant therapies.
Additionally, 2’,7’-Dichlorofluorescein is utilized in cellular imaging techniques due to its ability to penetrate cell membranes. Once inside the cells, it can react with intracellular ROS to emit fluorescence, thereby serving as a vital tool for visualizing cellular events and mechanisms in real-time. This application is especially pertinent in research involving cancer, neurodegenerative diseases, and aging, where oxidative stress plays a significant role.
In environmental science, DCF finds application as a marker to assess the oxidative potential of various environmental samples. It helps in evaluating the presence of pollutants and their impact on oxidative stress in aquatic ecosystems. This is achieved by measuring the fluorescence signal resulting from the interaction between DCF and ROS in the sample, which provides insights into the sample’s oxidative properties.
Lastly, DCF is instrumental in the pharmaceutical industry, particularly in drug development and screening. By using DCF-based assays, researchers can rapidly assess the oxidative properties of new drug compounds and their potential cytotoxic effects. This accelerates the identification of promising therapeutic agents and helps in optimizing their safety and efficacy profiles before clinical trials.
| XLogP3 | 4.7 |
| Hydrogen Bond Donor Count | 2 |
| Hydrogen Bond Acceptor Count | 5 |
| Rotatable Bond Count | 0 |
| Exact Mass | 399.9905288 g/mol |
| Monoisotopic Mass | 399.9905288 g/mol |
| Topological Polar Surface Area | 76Ų |
| Heavy Atom Count | 27 |
| Formal Charge | 0 |
| Complexity | 585 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 0 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently-Bonded Unit Count | 1 |
| Compound Is Canonicalized | Yes |
| PMID | Publication Date | Title | Journal |
|---|---|---|---|
| 34958783 | 2022-01-15 | Effect of major components of Tripterygium wilfordii Hook. f on the uptake function of organic anion transporting polypeptide 1B1 | Toxicology and applied pharmacology |
| 22910297 | 2012-11-01 | Oxidative effects of nanosecond pulsed electric field exposure in cells and cell-free media | Archives of biochemistry and biophysics |
| 22939937 | 2012-11-01 | Proinflammatory activation of macrophages by bisphenol A-glycidyl-methacrylate involved NFκB activation via PI3K/Akt pathway | Food and chemical toxicology : an international journal published for the British Industrial Biological Research Association |
| 22940460 | 2012-11-01 | Assessment of the role of in situ generated (E)-2,4-diene-valproic acid in the toxicity of valproic acid and (E)-2-ene-valproic acid in sandwich-cultured rat hepatocytes | Toxicology and applied pharmacology |
| 23022691 | 2012-11-01 | Nuclear targeting terpyridine iron(II) complexes for cellular imaging and remarkable photocytotoxicity | Journal of inorganic biochemistry |
| Publication Number | Title | Priority Date |
|---|---|---|
| CN-115177736-A | Tantalum amide nanoparticles with cartilage targeting and catalase activity and preparation method and use | 2022-07-20 |
| CN-115177746-A | Non-viral gene vector-transfected stem cell complex for the treatment of spinal cord injury | 2022-07-12 |
| CN-115068608-A | Phthalocyanine-artesunate oxygen-carrying liposome complex and its application in sonodynamics | 2022-06-22 |
| CN-114989189-A | A compound with aggregation-induced luminescence properties, preparation method and application thereof | 2022-06-06 |
| CN-114874346-A | A kind of lilac mushroom polysaccharide and its preparation method and application | 2022-05-23 |
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